Lyngbyabellin A

ID: ALA453207

Chembl Id: CHEMBL453207

Cas Number: 273202-85-0

PubChem CID: 10032587

Max Phase: Preclinical

Molecular Formula: C29H40Cl2N4O7S2

Molecular Weight: 691.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H]1NC(=O)CNC(=O)c2csc(n2)[C@H](C(C)(C)O)OC(=O)C(C)(C)[C@H](CCCC(C)(Cl)Cl)OC(=O)c2csc1n2

Standard InChI:  InChI=1S/C29H40Cl2N4O7S2/c1-8-15(2)20-23-34-17(14-43-23)25(38)41-18(10-9-11-29(7,30)31)27(3,4)26(39)42-21(28(5,6)40)24-33-16(13-44-24)22(37)32-12-19(36)35-20/h13-15,18,20-21,40H,8-12H2,1-7H3,(H,32,37)(H,35,36)/t15-,18-,20-,21+/m0/s1

Standard InChI Key:  VJSNPXXBMRWPEJ-CEDBRAGKSA-N

Alternative Forms

1. Parent:

   

   ALA453207

   LYNGBYABELLIN A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 691.70

Molecular Weight (Monoisotopic): 690.1715

AlogP: 5.52

#Rotatable Bonds: 7

Polar Surface Area: 156.81

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.65

CX Basic pKa:

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.25

Np Likeness Score: 1.89

References

1. Luesch H, Yoshida WY, Moore RE, Paul VJ, Mooberry SL..  (2000)  Isolation, structure determination, and biological activity of Lyngbyabellin A from the marine cyanobacterium lyngbya majuscula.,  63  (5): [PMID:10843570] [10.1021/np990543q]

2. Matthew S, Salvador LA, Schupp PJ, Paul VJ, Luesch H..  (2010)  Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam.,  73  (9): [PMID:20704304] [10.1021/np1004032]

3. PubChem BioAssay data set, 

4. Xu J, Zhang T, Yao J, Lu J, Liu Z, Ding L..  (2020)  Recent advances in chemistry and bioactivity of marine cyanobacteria Moorea species.,  201  [PMID:32652435] [10.1016/j.ejmech.2020.112473]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays